Some interesting points there, I think a couple of these are due to my interpretation of the English verbs, and some of them are used in a 'loose' sense here:-

Whatever happens, I'll leave it all to chance
I took this to mean 'whatever happens (and many things will happen, again and again,) I will always take the same approach, ie I will repeatedly, habitually 'leave it all to chance'.
Yes, if so that should have been "буду оставлять"; I somehow forgot the tense!

learning = учусь
This (to me) is an example of purposeful use of fairly poor English; I think what he really means is 'I realise...' But choosing a slightly incorrect verb implies the idea of being unsophisticated, an underdog, ill prepared and maybe even uneducated, but 'with his heart in the right place.' Maybe knowingly playing to the audience's feelings about themselves? He was a very astute writer, afterall.

Fairytales of yesterday will grow but never die
Duh. Can't believe I missed those. I suppose I was thinking of an endless stream of fairytales, continuously growing, etc; and 'not dying' as being (by definition) an ongoing state of no 'action', with no result. Dunno now!

I'll face it with a grin
This to me implies, like the case of 'leave it to chance' above, that he is stating how he intends to approach all adversity in future. So personally, I see that as continuously facing things, rather than facing something, then dealing with it, and then moving on to another thing.

I can't honestly say I know my own language that well, let alone anyone elses, so feel free to point out where I'm wrong, as I expect to have 'missed the point' at least a few times.
And thanks for the interest, too.